title: Remote aryl cyanation via isocyanide-cyanide rearrangement on tosylmethyl isocyanide derivatives.
abstract: The reaction of alkyl tosylmethyl isocyanides and 2-bromobenzyl bromides in the presence of t-BuLi gives rise to a cascade reaction to give unexpected 2-substituted 2,3-dihydro-1H-indenimines which, upon treatment with t-BuOK, rearrange to 2-vinylbenzonitriles in high overall yields. This simple procedure represents a new approach to the synthesis of aromatic nitriles via isocyanide-cyanide interconversion.
authors.affiliation: Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, 28871 - Alcalá de Henares, Madrid, Spain.
authors.forename: Anna
authors.initials: A
authors.lastname: Coppola
authors.forename: Patricia
authors.initials: P
authors.lastname: Sánchez-Alonso
authors.forename: David
authors.initials: D
authors.lastname: Sucunza
authors.forename: Carolina
authors.initials: C
authors.lastname: Burgos
authors.forename: Ramón
authors.initials: R
authors.lastname: Alajarín
authors.forename: Julio
authors.initials: J
authors.lastname: Alvarez-Builla
authors.forename: Marta E G
authors.initials: ME
authors.lastname: Mosquera
authors.forename: Juan J
authors.initials: JJ
authors.lastname: Vaquero